2008•The Journal of Organic ChemistryOpen access

Alkylation of 2-Substituted (6-Methyl-2-pyridyl)methyllithium Species with Epoxides

James R. Vyvyan, Rebecca C. Brown, Brian P. Woods

Abstract

Substituted (6-methyl-2-pyridyl)methyllithium species were reacted with 1,2-epoxyoctane and 2-methyl-2,3-epoxynonane. The monosubstituted epoxide reacted efficiently with lutidyllithium and a number of 2-substituted (6-methyl-2-pyridyl)methyllithium derivatives. The trisubstituted epoxide gave low yields of adducts with all (2-pyridyl)methyllithium species studied. These results are discussed in the context of a proposed synthesis of cananodine.

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Key concepts: Methyllithium, Epoxide, Alkylation, Context (archaeology), Chemistry, Adduct, Stereochemistry, Medicinal chemistry